5,6-Dichloronicotinic acid → Tert-butyl {4-[5-(5,6-dichloropyridin-3-yl)-1,2,4-oxadiazol-3-yl]-2-fluorophenoxy}acetate

HRID 219931Notes

Reaction equation

HRID 219931 reaction equation
[NH2:1][C:2](=[N:19][OH:20])[C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:5]([F:18])[CH:4]=1.[Cl:21][C:22]1[C:23]([Cl:31])=[N:24][CH:25]=[C:26]([CH:30]=1)[C:27](O)=O>>[Cl:21][C:22]1[CH:30]=[C:26]([C:27]2[O:20][N:19]=[C:2]([C:3]3[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])=[C:5]([F:18])[CH:4]=3)[N:1]=2)[CH:25]=[N:24][C:23]=1[Cl:31]

Participants

3

Reactant 2

HCID 2479875,6-Dichloronicotinic acidHCID 72307490Tert-butyl {4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}acetate

Product 1

HCID 86645655Tert-butyl {4-[5-(5,6-dichloropyridin-3-yl)-1,2,4-oxadiazol-3-yl]-2-fluorophenoxy}acetate

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 49 (995.01 mg; 3.50 mmol) and 5,6-dichloronicotinic acid (806.4 mg; 4.2 mmol). The reaction mixture was evaporated. The crude product was dissolved in EtOAc and washed with NH4Cl sat, NaHCO3 sat, brine and dried over MgSO4. After evaporation of the solvents, the resulting solid was suspended in MeCN and filtrated, affording the title compound as an off-white solid. LC/MS (Method B): 420.3 (M−H)−. HPLC (Method A) Rt 5.72 min (Purity: 99.4%).

Workup

  1. customThe title compound was prepared following procedure
  2. customThe reaction mixture was evaporated
  3. dissolutionThe crude product was dissolved in EtOAc
  4. washwashed with NH4Cl
  5. dry with materialbrine and dried over MgSO4
  6. customAfter evaporation of the solvents
  7. filtrationfiltrated

Sources & evidence

ORD record
ord-64d62b24c1d7405aa1b1f815f1046f9c
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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